Open AccessSyringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-Tg Polymeric Materials
Author(s) -
Angela L. Holmberg,
Kaleigh H. Reno,
Ngoc A. Nguyen,
Richard P. Wool,
Thomas H. Epps
Publication year - 2016
Publication title -
acs macro letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.966
H-Index - 92
ISSN - 2161-1653
DOI - 10.1021/acsmacrolett.6b00270
Subject(s) - monomer , methacrylate , polymerization , chain transfer , macromolecule , polymer , lignin , materials science , polymer chemistry , glass transition , chemical engineering , hardwood , organic chemistry , radical polymerization , chemistry , composite material , ecology , biochemistry , engineering , biology
As viable precursors to a diverse array of macromolecules, biomass-derived compounds must impart wide-ranging and precisely controllable properties to polymers. Herein, we report the synthesis and subsequent reversible addition-fragmentation chain-transfer polymerization of a new monomer, syringyl methacrylate (SM, 2,6-dimethoxyphenyl methacrylate), that can facilitate widespread property manipulations in macromolecules. Homopolymers and heteropolymers synthesized from SM and related monomers have broadly tunable and highly controllable glass transition temperatures ranging from 114 to 205 °C and zero-shear viscosities ranging from ∼0.2 kPa·s to ∼17,000 kPa·s at 220 °C, with consistent thermal stabilities. The tailorability of these properties is facilitated by the controlled polymerization kinetics of SM and the fact that one vs two o -methoxy groups negligibly affect monomer reactivity. Moreover, syringol, the precursor to SM, is an abundant component of depolymerized hardwood (e.g., oak) and graminaceous (e.g., switchgrass) lignins, making SM a potentially sustainable and low-cost candidate for tailoring macromolecular properties.